2-Hydroxybenzaldehyde
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Basic Info
| Common Name | 2-Hydroxybenzaldehyde(F05588) |
| 2D Structure | |
| Description | 2-Hydroxybenzaldehyde is found in common buckwheat. 2-Hydroxybenzaldehyde is present in cinnamon (Cinnamomum versum). 2-Hydroxybenzaldehyde is a flavouring ingredient. |
| FRCD ID | F05588 |
| CAS Number | 90-02-8 |
| PubChem CID | 6998 |
| Formula | C7H6O2 |
| IUPAC Name | 2-hydroxybenzaldehyde |
| InChI Key | SMQUZDBALVYZAC-UHFFFAOYSA-N |
| InChI | InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H |
| Canonical SMILES | C1=CC=C(C(=C1)C=O)O |
| Isomeric SMILES | C1=CC=C(C(=C1)C=O)O |
| Synonyms |
o-Hydroxybenzaldehyde
SALICYLALDEHYDE
2-Hydroxybenzaldehyde
90-02-8
o-Formylphenol
Salicylal
2-Formylphenol
Benzaldehyde, 2-hydroxy-
Salicylic aldehyde
Salicyladehyde
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Aldehydes - Aryl-aldehydes - Benzaldehydes |
| Direct Parent | Hydroxybenzaldehydes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Hydroxybenzaldehyde - Benzoyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Vinylogous acid - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 122.123 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 101 |
| Monoisotopic Mass | 122.037 |
| Exact Mass | 122.037 |
| XLogP | 1.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9344 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.9351 |
| P-glycoprotein Substrate | Non-substrate | 0.8033 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9458 |
| Non-inhibitor | 0.9855 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8808 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9067 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7932 |
| CYP450 2D6 Substrate | Non-substrate | 0.8793 |
| CYP450 3A4 Substrate | Non-substrate | 0.7523 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6301 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9801 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9552 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6464 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9503 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8545 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9110 |
| Non-inhibitor | 0.9747 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8136 |
| Fish Toxicity | High FHMT | 0.7790 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9663 |
| Honey Bee Toxicity | High HBT | 0.7680 |
| Biodegradation | Ready biodegradable | 0.8515 |
| Acute Oral Toxicity | III | 0.8407 |
| Carcinogenicity (Three-class) | Non-required | 0.6665 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.7978 | LogS |
| Caco-2 Permeability | 1.9293 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3639 | LD50, mol/kg |
| Fish Toxicity | 0.4870 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3241 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Synthesis, characterization, X-ray structure and biological activities of C-5-bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene. | Molecules | 2013 Oct 29 | 24172244 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]